The reduction of aromatic hydrocarbons by alkali metals is known to generate reactive, organic radicals. These organic radicals are widely used reagents employed in a number of chemical reactions including, but not limited to, polymerization initiation, reductive metalation, ketyl-alkene cyclizations, lactone deprotonation, and reductive bond cleavage. These reagents are also important for modeling graphitic battery materials and are electrically conductive in solution. However, a notable drawback of these compounds is that they are very sensitive, rarely isolated, and must be prepared immediately prior to use. Their sensitivity and solution behavior complicates their use as chemical reagents and impedes their commercial sale.
Thus, additional stable alkali metal arene radical anion compositions and method of making such are needed.